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Regional Re-entry Support Specialist

For Vermont Works for Women


Position Summary:

VWW is hiring for two regional, remote positions in southern VT; one focused in the Rutland area, and the other in the Brattleboro area. Both positions will require some travel around the region between southern hub areas including Rutland, Springfield, Bennington & Brattleboro. The primary responsibility of both positions is to support incarcerated women and women reentering the community to ameliorate the impact of COVID-19 that has required isolation of some incarcerated individuals, and to limit the in-person contacts of re-entering individuals. This position will provide recently released women with coaching and intensive case management supports focused on helping women secure and maintain employment to become self-sufficient and productive members of the community. Key components involve creating motivating supports sensitive to the needs and challenges of incarcerated women, and working collaboratively with contacts at the Chittenden Regional Correctional Facility, partner organizations, regional resource providers, community justice centers, employers, and members of the VWW team. This is a temporary position, ending on December 20, 2020.

Essential Functions:

Direct Service: 60% of total time

  • Participate remotely in release planning meetings at CRCF to be introduced to women being released to the region
  • Connect recently released women with local resources and help establish relationships with providers in their local communities 
  • Provide work-readiness training and job seeking support 
  • Consistent follow up with women in the community to remain engaged and connected
  • Evaluate emergent needs of released women and provide supports and supplies to help women secure or maintain employment (such as work appropriate clothing or work-required clothing, transportation costs, first month cell phone bill or internet bill, and other miscellaneous expenses)
  • Provide consistent feedback to participants, supporting their emotional and professional growth of participants
  • Provide transitional support as needed throughout employment onboarding to problem solve crisis and obstacles improving job retention


Community & Relationship Development: 30% of total time

  • Develop VWW relationships with regional Community Justice Centers 
  • Connect with and establish relationships with employers in the region 
  • Establish connections and contacts at local resource providers
  • Engage with and develop volunteer networks in the region
  • Attend relevant in-person and remote meetings as necessary
  • Participation with statewide Re-Entry Coalition


Additional Duties & Responsibilities: 10% of total time

  • Record and document case notes, participant skill gains & progress in VWW databases
  • Attendance at occasional morning & weekend meetings and necessary events
  • Other duties as assigned


Education & Experience:

  • Relevant experience and strong interest in human services, social services, social justice, criminal justice
  • Experience with direct service, coaching/mentoring, & program delivery


Specialized Skills, Knowledge, Licenses, etc.

  • Interpersonal skills; conflict resolution, motivational interviewing, coaching methods
  • Effective communicator with diverse populations
  • Understanding of effects of poverty, trauma, and incarceration on women
  • Passion for social justice and empowering others to achieve their potential
  • Small group training or facilitation
  • Experience and/or training in Microsoft Office including Word, Excel, Outlook and Teams


Schedule and work environment

  • Schedule will be primarily Monday-Friday with varying hours
  • This is a remote position stationed in southern Vermont, with reliable transportation needed for significant travel required between the southern hubs of Rutland, Springfield, Bennington & Brattleboro
  • Ability to sit and/or stand for 7-8 hrs/day
  • Must be able to occasionally lift and/or move up to 50 lbs.
  • Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.


Success Factors (i.e. personal characteristics that contribute to excelling in position):

  • Clear commitment to, and enthusiasm for, VWW’s mission.
  • Commitment to engaging in efforts to improve our work internally and externally with diverse individuals and groups.
  • Positive, cooperative team spirit.
  • Excellent people skills, with experience collaborating in a multi-disciplinary, diverse, and dynamic team.
  • Ability to receive and give constructive feedback.
  • Demonstrated resourcefulness in setting priorities, proposing new ways of creating efficiencies, and guiding investment in people and systems.
  • Excellent communication skills, both written and verbal.
  • A sense of humor, tact and diplomacy.
  • Ability to lead and train staff, participants, and/or volunteers.
  • Ability to deal with the public and staff in a friendly, pleasant and professional manner.
Jul 14, 2020
Accepting applications through July 31.
Women's Programs
Remote positions; one focused in Rutland area and the other in the Brattleboro area.
Part-time (25 hours a week), non-exempt.
To apply, please email a PDF copy of your resume and cover letter to If reasonable accommodation is needed to participate in the job application or interview process, please email